Tell me you love me
By BillyBoy 19 Jan 2022
He was great. He followed all my requests. A dream come true.
Gay Crossdresser Stories
GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressing up as women and gay sex with transvestites and crossdressers.
Crossdresser makes homeless man happy
By Paulacd 17 Jan 2022
I had gotten dressed very sexy and slutty one night being completely hairless permanently except for my eyebrows eyelashes and long hair on my head.
Becoming a sissy crossdresser for him
By BillyBoy 15 Jan 2022
I started wearing moms underclothes when I was younger. They were always laying around in her bedroom and in the laundry. But later I discovered he was leaving them around for me to find. He was tricking me into becoming a sissy crossdresser for him.
Heather (ch. 5)
By Heather_xd 11 Jan 2022
Apologies for delay in the next chapter of Heather - The last chapter finished with my live in lover finding me being spanked by my coloured friend after he had fucked me and the cum was dripping from my pussy. He packed and left straight away.
Neighborhood faggot boy (ch. 2)
By Alleykat 11 Jan 2022
Every old pervert knows where I live and now I'm the neighborhood cocksucking cumloving slut
Prom going wrong
By BillyBoy 11 Jan 2022
I dressed like a girl for prom. My friend Jeff and I didn't have proper girl dates. It was sort of a joke and a few of the other boys were doing it. And Jeff's dad seemed to like me a lot.
The Struggles of Becoming a Woman
By Getoutofmymind 11 Jan 2022
When becoming a woman things, in the beginning, are extremely difficult! Chapter 1.
Blackmail
By Victor 10 Jan 2022
Decker has found out his nemesis, Fitch, another closeted jock, has been hooking up with a male escort/cam boy. Now he intends to get what he wants from the gorgeous jock by blackmailing him.
I'm his bound and gagged girlfriend
By BillyBoy 6 Jan 2022
She told her friends I wanted to wear her underwear and be tied up when we had sex. It was a weak moment for me. I shouldn't have asked her. I was young and didn't know any better. She didn't appreciate my wishes at all. That was it for her, and most any other chance I may have had with a girl. But, she handed me off to someone who did appreciate my fantasy. For better or worse!
After Halloween
By BillyBoy 30 Dec 2021
I wore a girl's dress as a joke to a Halloween party. It was all in fun. Wives and girlfriends were there. But after that, I got a few uncomfortable calls and texts from a few of the men who saw me.
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bondage blowjob
By BillyBoy 28 Dec 2021
I woke up in his bedroom, wearing his wife's wedding lingerie. I'm on my knees with his cock in my face. What now?
First Time Adult Book Store Wearing Panties
By CuriousInPanties63 24 Dec 2021
The first time I wore panties to an adult book store at 19 years old and an older sexy daddy man in his 60's had some fun with me in my panties.
Neighborhood faggot boy
By Alleykat 24 Dec 2021
My address was on the bathroom stall.. Cocksucking cumloving pretty boy cruise by after 9pm weekends
Cross dresser.. Twink.. Tranny?
By djfmonkey 22 Dec 2021
My straight buddy and I visit a gay bar, where we discover our own inner selves, and the truth about each other
Shower Power
By BillyBoy 22 Dec 2021
'Daddy' shaved me in the shower. While the water was pouring over us, he put me in a matching set of rubbery vintage Playtex bra and open bottom girdle panties.
Chis(topher) & Chris(tina) (ch. 3)
By djfmonkey 12 Dec 2021
Chris and I finally visit my parents for the holidays in my overly homophobic upstate New York Hometown
Secret Sissy
By BillyBoy 10 Dec 2021
I've been in the closet all my life. Finally, I have a chance to try out being a sissy girl for a real man
Dreams and Frustration
By BillyBoy 9 Dec 2021
Every day I awake from a dream of being used as a girl whore. I can't stop it. I'm in trouble!
My secret dreams
By BillyBoy 7 Dec 2021
The gay date I'd love to experience. I've had a few gay experiences, but someday a man will make me his little bitch. I'd love that!
Halloween party
By BillyBoy 2 Dec 2021
I finally let him seduce me. I agree to meet him. He has been flirting and making promises. Then at the last minute, he tells me I'm going to dress like a woman tonight.
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Park Slut (ch. 3)
By Alleykat 30 Nov 2021
Turned into the park cocksucker by a fat old man
Jessi’s debut - A true Jessi story
By JohnRain24601 25 Nov 2021
John goes out as Jessi for the first time - to a party at an adult book store.
Chis(topher) & Chris(tina) (ch. 2)
By djfmonkey 23 Nov 2021
Chapter 2. - Chris and I meet the grandparents
Park Slut (ch. 3)
By Alleykat 23 Nov 2021
I would go to the park at night letting guys blow me until the fat old man turned me into the cocksucking cumloving slut at the park and at my mom's house.
Chis(topher) & Chris(tina)
By djfmonkey 22 Nov 2021
I met and fell for a crossdresser, explore chapter 1 introducing us, and future chapters meeting family and friends
Now I'm a crossdressing Domme?
By BillyBoy 20 Nov 2021
A shy, submissive guy hits me up to dress like his wife and Domme him. I actually liked it more than I thought I would!
How this straight guy became a sissy bottom
By Somewhat Straight 17 Nov 2021
It took while, but my transformation is complete
Doctors are human too
By BillyBoy 11 Nov 2021
I forgot and wore some panties to my check-up. The doc was surprised. But he responded differently than I expected.
blow and go buddy gets kinky
By BillyBoy 10 Nov 2021
Joe was always pretty much a Dom. But he seemed to figure out I'd do pretty much anything to suck him off. So he just keeps pushing. Now I have to go out and buy some items he requested. And that is a whole other story!
In a short span I became a sissy boy trap (ch. 2)
By Desertbiguy 10 Nov 2021
I had spent all of my time getting indoctrinated in gay sex by Tom G. I forgot about my first man to pop my anal cherry Mark.
Introduction into Gay Domination (ch. 2)
By Anthony 8 Nov 2021
I went to work and tried not to run into Jerry, but that was hard, seemed like Jerry kept looking over at me and would walk by me giving me a look. When no one was around, he would come up to me and show me a picture of me on his phone of me in one of the positions that I was in.
Tranny at the bar
By djfmonkey 8 Nov 2021
The best looking girl in the bar was a guy and I love her.
Nanny cam gone bad
By BillyBoy 5 Nov 2021
My wife installed one of those nanny cams. She wanted to see what the dog was doing when we were at work. She didn't tell me. She started watching me dress in her underclothes and tie myself up like a kidnap victim, jerking off. Not sure what to do, she asked a friend to watch the videos. He knew just what to do with me.
Crossdressing
By BillyBoy 2 Nov 2021
Envious of the girls always getting to wear those cute little bras and panties.
Halloween is a great time to express sexual feelings
By Desertbiguy 2 Nov 2021
I decided to dress up as a girl for halloween. There was a big party going on for us jr high kids. And looked good. Maybe to good. Mark was a good looking guy. Something happened at party. He became attracted to me.